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The Best Chelsea Boots You Can Buy

From best-value to best-in-class, our guide to Chelsea boots covers ready-made designs from new brands and bespoke pairs from legacy makers.


Chelsea boots originated in England in the mid-19th century. Then, they were called "Paddock boots," a short style for equestrian functions. They've only strayed from home — and horse riding — just recently. The elasticized wonders were a staple in mid-’60s London scenes and protected the feet of seemingly every British invader — from John Lennon to Ringo Starr. Recently, they’ve seen a revival on many of menswear’s best-dressed.

What Are Chelsea Boots?

Marked by a slim silhouette, elastic side panels, and heel pull-tabs, the boot has seen reinterpretations in leather, suede, and neoprene, either with crepe, leather or rubber soles. They're a versatile option that's gone largely unchanged since inception, save for material swaps here and there. And while they aren't as in-demand as they were in the mid-2010s — when everyone from Kanye West and David Beckham to Harry Styles and Justin Theroux was wearing theirs — Chelsea boots prove sensible now more than ever. The style emphasizes both aesthetics and comfortability, meeting in a middle ground where both camps — those wearing them for their look and those wearing them for their convenience — are appeased.

How to Wear Chelsea Boots

Further, designers from all over have riffed on the shape over and over and over again, resulting in a rich landscape of iterations to choose from. Whether you're looking for a pair that's polished or preppy (to wear with an Oxford and chinos), with a bit of street cred (to wear with jeans and a hoodie) or suit-friendly (to wear with a, well, suit), here are more than a dozen different Chelsea boots to choose from.

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Best Overall Chelsea Boots
Blundstone BL558 Boots
Best Upgrade Chelsea Boots
R.M. Williams Craftsman Boot
Best Affordable Chelsea Boots
Rhodes Blake Boot
New Republic Sonoma Suede Chelsea Boot
Taylor Stitch The Ranch Boot
Viberg Chelsea Boot
Belstaff Longton Leather Chelsea Boot
Unmarked Chelsea Toro Special Edition
Oliver Cabell Chelsea Boot
Oak Street Bootmakers 5504 Chelsea Boot
Common Projects Suede Chelsea Boots
Diemme Balbi Suede Ankle Boots
Grant Stone Chelsea Boot
Astorflex Bitflex
Nisolo All-Weather Chelsea Boot
Beckett Simonon Bolton Chelsea Boots
Tecovas The Chance
Clarks Clarkdale Hall Beeswax Leather
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